Propionic Acid → HCID 66580430、化合物

HRID 1521873ノート

反応式

HRID 1521873 の反応式
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[S:22](=[O:25])(=[O:24])[CH2:23][C:14]=3[C:13]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])=[N:12]2)[CH:6]=1)[NH2:4].[C:34](O)(=O)[CH2:35][CH3:36]>CCOC(C)=O>[CH2:35]([C:36]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[C:7]([N:11]3[C:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[S:22](=[O:24])(=[O:25])[CH2:23][C:14]=4[C:13]([C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])=[N:12]3)[CH:8]=[CH:9][CH:10]=2)[N:4]=1)[CH3:34]

参加物

4

反応物 2

HCID 1032Propionic AcidHCID 86670899HCID 86670899、化合物

生成物 1

HCID 66580430HCID 66580430、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of N′-hydroxy-3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzenecarboximidamide (150 mg, 0.32 mmol) in dry EtOAc is added propionic acid (13 μl, 0.32 mmol) under nitrogen followed by TEA (0.13 mL, 0.963 mmol) and propane phosphonic acid cyclic anhydride (0.51 mL, 0.80 mmol) at 0° C. under nitrogen. The reaction mixture is heated to 80° C. for 12 h under nitrogen and concentrated under vacuum. Solid residue is purified by silica gel column chromatography (1.2% MeOH in DCM) to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.24-8.22 (d, J=7.4 Hz, 1H), 8.05-8.02 (m, 2H), 7.81-7.77 (m, 2H), 7.64 (m, 1H), 7.57 (m, 1H), 6.93-6.91 (d, J=7.9 Hz, 1H), 4.91 (s, 2H), 3.92-3.90 (m, 2H), 3.67 (m, 4H), 3.61-3.60 (m, 2H), 3.02-3.0 (m, 2H), 1.33-1.29 (t, J=7.6 Hz, 3H). MS (ESI+): 506.0. HPLC (max plot) 97.13%; Rt 4.34 min.

後処理

  1. concentrationconcentrated under vacuum
  2. customSolid residue is purified by silica gel column chromatography (1.2% MeOH in DCM)

出典と根拠

ORDレコード
ord-235733a77e0749a09e1dbc5a04b12a3e
出典データセット
uspto-grants-2015_07
特許番号
US09073940B2

反応ノート

読み込み中…